Tert-Butylamine → HCID 66878475, compound

HRID 1878397Notes

Reaction equation

HRID 1878397 reaction equation
[OH:1][CH:2]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)[CH:3]([CH3:5])[CH3:4].C(N(C(C)C)C(C)C)C.[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25]>CN(C)C=O>[C:24]([NH:28][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([CH:2]([OH:1])[CH:3]([CH3:4])[CH3:5])[CH:7]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 20763023HCID 20763023, compound

Product 1

HCID 66878475HCID 66878475, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(1-hydroxy-2-methylpropyl)benzoic acid (677 mg, 3.49 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyl uronium hexafluorophosphate (1.73 g, 4.54 mmol), N-ethyl-N-isopropylpropan-2-amine (1.21 mL, 6.97 mmol) and tert-butylamine (510 mg, 6.97 mmol) in N,N-dimethylformamide (12.0 mL) was subjected to microwave irradiation at 100° C. for 10 minutes. The reaction mixture was concentrated under vacuum and purified with silica column chromatography (eluting with 9% to 33% ethyl acetate in heptane) to afford the title compound (718 mg). MS (ESI) m/z 250.4 [M+H]+

Workup

  1. customirradiation at 100° C. for 10 minutes
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. custompurified with silica column chromatography (eluting with 9% to 33% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-9140152a6ee5412b9e7e12c493c50798
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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